#------------------------------------------------------------------------------
#$Date: 2023-10-10 00:57:42 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132192.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7132192
loop_
_publ_author_name
'Mondal, Sudeshna'
'Giri, Chandan Kumar'
'Baidya, Mahiuddin'
_publ_section_title
;
 Enaminone-directed ruthenium(II)-catalyzed C--H activation and annulation
 of arenes with diazonaphthoquinones for polycyclic benzocoumarins
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03999D
_journal_year                    2023
_chemical_formula_sum            'C18 H9 F3 O2'
_chemical_formula_weight         314.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-07-24 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                103.951(3)
_cell_angle_beta                 106.880(3)
_cell_angle_gamma                91.212(3)
_cell_formula_units_Z            6
_cell_length_a                   10.9295(9)
_cell_length_b                   11.7939(9)
_cell_length_c                   17.2156(13)
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.98
_cell_volume                     2050.9(3)
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4(Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2233
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            73634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     678
_refine_ls_number_reflns         7202
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.2058
_refine_ls_R_factor_gt           0.1169
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1699P)²+0.8357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2837
_refine_ls_wR_factor_ref         0.3493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             7202
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03999d2.cif
_cod_data_source_block           shelx
_cod_database_code               7132192
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5495(8) 0.2804(8) 0.5045(6) 0.103(4) Uani 1 1 d D U . . .
C2 C 0.5138(8) 0.2038(8) 0.4166(5) 0.064(2) Uani 1 1 d . . . . .
C3 C 0.4754(9) 0.0848(9) 0.3979(6) 0.082(3) Uani 1 1 d . . . . .
H3 H 0.468314 0.051404 0.440291 0.098 Uiso 1 1 calc R U . . .
C4 C 0.4480(8) 0.0169(8) 0.3178(7) 0.078(3) Uani 1 1 d . . . . .
H4 H 0.426153 -0.063409 0.306076 0.094 Uiso 1 1 calc R U . . .
C5 C 0.4527(6) 0.0673(6) 0.2537(5) 0.0524(18) Uani 1 1 d . . . . .
C6 C 0.4342(7) -0.0127(7) 0.1702(5) 0.061(2) Uani 1 1 d . . . . .
C7 C 0.4809(6) 0.1552(5) 0.1231(4) 0.0435(16) Uani 1 1 d . . . . .
C8 C 0.5016(7) 0.1849(7) 0.0540(4) 0.058(2) Uani 1 1 d . . . . .
H8 H 0.502814 0.127095 0.006780 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5197(7) 0.2981(7) 0.0575(4) 0.0539(19) Uani 1 1 d . . . . .
H9 H 0.538294 0.318185 0.012858 0.065 Uiso 1 1 calc R U . . .
C10 C 0.5120(6) 0.3891(6) 0.1256(4) 0.0441(16) Uani 1 1 d . . . . .
C11 C 0.5189(7) 0.5074(7) 0.1243(5) 0.059(2) Uani 1 1 d . . . . .
H11 H 0.538328 0.527548 0.079941 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4981(8) 0.5931(6) 0.1859(5) 0.067(2) Uani 1 1 d . . . . .
H12 H 0.504752 0.671259 0.184344 0.080 Uiso 1 1 calc R U . . .
C13 C 0.4665(7) 0.5630(6) 0.2514(5) 0.0583(19) Uani 1 1 d . . . . .
H13 H 0.447270 0.621283 0.291959 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4631(6) 0.4503(5) 0.2576(4) 0.0459(16) Uani 1 1 d . . . . .
H14 H 0.444683 0.433700 0.303344 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4870(6) 0.3575(5) 0.1956(4) 0.0365(14) Uani 1 1 d . . . . .
C16 C 0.4833(6) 0.2353(5) 0.1971(4) 0.0404(15) Uani 1 1 d . . . . .
C17 C 0.4828(6) 0.1900(5) 0.2689(4) 0.0410(15) Uani 1 1 d . . . . .
C18 C 0.5162(6) 0.2552(6) 0.3527(4) 0.0474(17) Uani 1 1 d . . . . .
H18 H 0.540596 0.335220 0.365883 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9132(9) 0.2432(6) 0.7770(6) 0.069(2) Uani 1 1 d . . . . .
C20 C 0.8830(6) 0.3399(5) 0.8380(4) 0.0477(17) Uani 1 1 d . . . . .
C21 C 0.8409(7) 0.3171(7) 0.9033(6) 0.067(2) Uani 1 1 d . . . . .
H21 H 0.832438 0.240870 0.908480 0.080 Uiso 1 1 calc R U . . .
C22 C 0.8129(7) 0.4080(9) 0.9585(5) 0.068(2) Uani 1 1 d . . . . .
H22 H 0.788805 0.394046 1.003175 0.082 Uiso 1 1 calc R U . . .
C23 C 0.8195(6) 0.5208(7) 0.9496(4) 0.0491(18) Uani 1 1 d . . . . .
C24 C 0.7996(7) 0.6180(10) 1.0162(4) 0.068(2) Uani 1 1 d . . . . .
C25 C 0.8417(6) 0.7524(6) 0.9416(4) 0.0519(18) Uani 1 1 d . . . . .
C26 C 0.8525(7) 0.8728(7) 0.9470(6) 0.073(3) Uani 1 1 d . . . . .
H26 H 0.850265 0.927433 0.995473 0.087 Uiso 1 1 calc R U . . .
C27 C 0.8660(7) 0.9075(6) 0.8818(7) 0.073(3) Uani 1 1 d . . . . .
H27 H 0.878335 0.987392 0.886386 0.087 Uiso 1 1 calc R U . . .
C28 C 0.8620(6) 0.8260(6) 0.8055(5) 0.056(2) Uani 1 1 d . . . . .
C29 C 0.8660(7) 0.8630(7) 0.7325(7) 0.069(3) Uani 1 1 d . . . . .
H29 H 0.879730 0.942577 0.736434 0.083 Uiso 1 1 calc R U . . .
C30 C 0.8500(8) 0.7842(8) 0.6589(7) 0.075(3) Uani 1 1 d . . . . .
H30 H 0.853971 0.809613 0.612460 0.090 Uiso 1 1 calc R U . . .
C31 C 0.8280(7) 0.6668(7) 0.6512(5) 0.059(2) Uani 1 1 d . . . . .
H31 H 0.814001 0.613348 0.599263 0.070 Uiso 1 1 calc R U . . .
C32 C 0.8266(6) 0.6277(5) 0.7193(4) 0.0434(16) Uani 1 1 d . . . . .
H32 H 0.811092 0.547511 0.712343 0.052 Uiso 1 1 calc R U . . .
C33 C 0.8473(6) 0.7028(5) 0.7989(4) 0.0380(15) Uani 1 1 d . . . . .
C34 C 0.8473(6) 0.6666(5) 0.8727(4) 0.0364(14) Uani 1 1 d . . . . .
C35 C 0.8510(5) 0.5466(5) 0.8820(3) 0.0344(14) Uani 1 1 d . . . . .
C36 C 0.8876(5) 0.4526(5) 0.8282(4) 0.0334(14) Uani 1 1 d . . . . .
H36 H 0.915462 0.466764 0.784935 0.040 Uiso 1 1 calc R U . . .
C37 C 0.1710(6) 0.4442(5) 0.6062(4) 0.067(2) Uani 1 1 d D U . . .
C38 C 0.1718(6) 0.5490(5) 0.6764(4) 0.0392(15) Uani 1 1 d . . . . .
C39 C 0.1618(6) 0.5337(6) 0.7522(4) 0.0496(18) Uani 1 1 d . . . . .
H39 H 0.155192 0.459077 0.760519 0.060 Uiso 1 1 calc R U . . .
C40 C 0.1619(6) 0.6318(6) 0.8141(4) 0.0511(18) Uani 1 1 d . . . . .
H40 H 0.155132 0.623543 0.865083 0.061 Uiso 1 1 calc R U . . .
C41 C 0.1720(6) 0.7425(5) 0.8019(4) 0.0370(14) Uani 1 1 d . . . . .
C42 C 0.1837(6) 0.8413(7) 0.8752(4) 0.0512(18) Uani 1 1 d . . . . .
C43 C 0.2198(6) 0.9683(5) 0.7916(4) 0.0472(17) Uani 1 1 d . . . . .
C44 C 0.2567(7) 1.0854(6) 0.7962(6) 0.065(2) Uani 1 1 d . . . . .
H44 H 0.277484 1.141964 0.847312 0.078 Uiso 1 1 calc R U . . .
C45 C 0.2617(7) 1.1150(6) 0.7270(6) 0.069(2) Uani 1 1 d . . . . .
H45 H 0.290628 1.191561 0.730931 0.082 Uiso 1 1 calc R U . . .
C46 C 0.2240(7) 1.0324(6) 0.6482(5) 0.059(2) Uani 1 1 d . . . . .
C47 C 0.2222(8) 1.0632(7) 0.5729(7) 0.072(3) Uani 1 1 d . . . . .
H47 H 0.254157 1.138547 0.576385 0.087 Uiso 1 1 calc R U . . .
C48 C 0.1756(10) 0.9861(8) 0.4964(7) 0.084(3) Uani 1 1 d . . . . .
H48 H 0.180603 1.006869 0.448522 0.100 Uiso 1 1 calc R U . . .
C49 C 0.1211(9) 0.8780(7) 0.4902(5) 0.073(2) Uani 1 1 d . . . . .
H49 H 0.080914 0.828415 0.437240 0.087 Uiso 1 1 calc R U . . .
C50 C 0.1243(7) 0.8407(6) 0.5600(4) 0.0513(18) Uani 1 1 d . . . . .
H50 H 0.088658 0.765459 0.553702 0.062 Uiso 1 1 calc R U . . .
C51 C 0.1808(6) 0.9147(5) 0.6418(4) 0.0443(16) Uani 1 1 d . . . . .
C52 C 0.1916(6) 0.8806(5) 0.7180(4) 0.0394(15) Uani 1 1 d . . . . .
C53 C 0.1790(5) 0.7588(5) 0.7251(4) 0.0331(13) Uani 1 1 d . . . . .
C54 C 0.1816(6) 0.6591(5) 0.6632(4) 0.0351(14) Uani 1 1 d . . . . .
H54 H 0.189961 0.666859 0.612454 0.042 Uiso 1 1 calc R U . . .
O1 O 0.4040(6) -0.1178(4) 0.1502(4) 0.091(2) Uani 1 1 d . . . . .
O2 O 0.4624(5) 0.0357(4) 0.1123(3) 0.0592(13) Uani 1 1 d . . . . .
O3 O 0.7692(6) 0.6032(7) 1.0755(3) 0.101(2) Uani 1 1 d . . . . .
O4 O 0.8236(5) 0.7271(5) 1.0125(3) 0.0715(16) Uani 1 1 d . . . . .
O5 O 0.1714(5) 0.8360(5) 0.9409(3) 0.0745(17) Uani 1 1 d . . . . .
O6 O 0.2198(5) 0.9488(4) 0.8671(3) 0.0585(13) Uani 1 1 d . . . . .
F1 F 0.5678(16) 0.2173(10) 0.5595(6) 0.136(5) Uani 0.692(16) 1 d D U P A 1
F2 F 0.4652(13) 0.3537(14) 0.5193(7) 0.161(7) Uani 0.692(16) 1 d D U P A 1
F3 F 0.6593(12) 0.3470(12) 0.5250(6) 0.131(5) Uani 0.692(16) 1 d D U P A 1
F1' F 0.4441(18) 0.261(3) 0.5254(16) 0.133(8) Uani 0.308(16) 1 d D U P A 2
F2' F 0.566(3) 0.3950(10) 0.5171(13) 0.129(9) Uani 0.308(16) 1 d D U P A 2
F3' F 0.644(2) 0.253(3) 0.5624(13) 0.133(10) Uani 0.308(16) 1 d D U P A 2
F4 F 0.9726(6) 0.1618(4) 0.8124(4) 0.115(2) Uani 1 1 d . . . . .
F5 F 0.9896(6) 0.2751(4) 0.7383(4) 0.111(2) Uani 1 1 d . . . . .
F6 F 0.8108(6) 0.1838(5) 0.7177(4) 0.111(2) Uani 1 1 d . . . . .
F7 F 0.188(2) 0.3473(9) 0.6307(9) 0.108(5) Uani 0.63(3) 1 d D U P B 1
F8 F 0.2641(16) 0.4590(11) 0.5731(11) 0.088(4) Uani 0.63(3) 1 d D U P B 1
F9 F 0.0637(12) 0.4244(14) 0.5430(10) 0.111(6) Uani 0.63(3) 1 d D U P B 1
F9' F 0.0553(13) 0.388(2) 0.576(2) 0.122(8) Uani 0.37(3) 1 d D U P B 2
F7' F 0.251(3) 0.370(2) 0.6325(16) 0.109(8) Uani 0.37(3) 1 d D U P B 2
F8' F 0.199(4) 0.4682(17) 0.5423(14) 0.103(7) Uani 0.37(3) 1 d D U P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 F2 107.4(7) . . ?
F2' C1 F3' 106.2(9) . . ?
F1 C1 F3 105.3(7) . . ?
F2 C1 F3 105.2(8) . . ?
F2' C1 F1' 105.0(9) . . ?
F3' C1 F1' 104.8(8) . . ?
F1 C1 C2 111.2(9) . . ?
F2 C1 C2 114.8(8) . . ?
F2' C1 C2 119.2(11) . . ?
F3' C1 C2 118.4(13) . . ?
F3 C1 C2 112.3(8) . . ?
F1' C1 C2 101.2(12) . . ?
C18 C2 C3 119.9(8) . . ?
C18 C2 C1 118.3(7) . . ?
C3 C2 C1 121.8(7) . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.0(8) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C17 121.6(8) . . ?
C4 C5 C6 117.1(7) . . ?
C17 C5 C6 121.2(6) . . ?
O1 C6 O2 117.6(8) . . ?
O1 C6 C5 126.2(8) . . ?
O2 C6 C5 116.1(6) . . ?
O2 C7 C16 122.2(6) . . ?
O2 C7 C8 113.1(6) . . ?
C16 C7 C8 124.6(6) . . ?
C9 C8 C7 118.1(7) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 123.2(7) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C11 C10 C9 122.2(6) . . ?
C11 C10 C15 119.5(6) . . ?
C9 C10 C15 118.2(6) . . ?
C12 C11 C10 121.8(7) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 121.6(7) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 121.4(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 116.4(6) . . ?
C14 C15 C16 124.6(6) . . ?
C10 C15 C16 119.0(6) . . ?
C7 C16 C15 115.9(6) . . ?
C7 C16 C17 117.9(6) . . ?
C15 C16 C17 126.2(6) . . ?
C18 C17 C5 116.2(6) . . ?
C18 C17 C16 126.1(6) . . ?
C5 C17 C16 117.6(6) . . ?
C2 C18 C17 121.8(7) . . ?
C2 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
F5 C19 F6 106.4(8) . . ?
F5 C19 F4 104.7(8) . . ?
F6 C19 F4 104.1(6) . . ?
F5 C19 C20 114.5(6) . . ?
F6 C19 C20 113.7(7) . . ?
F4 C19 C20 112.6(7) . . ?
C36 C20 C21 119.8(7) . . ?
C36 C20 C19 119.8(6) . . ?
C21 C20 C19 120.3(7) . . ?
C22 C21 C20 119.0(7) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 121.2(7) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C35 121.9(7) . . ?
C22 C23 C24 118.7(7) . . ?
C35 C23 C24 119.3(7) . . ?
O3 C24 O4 118.6(8) . . ?
O3 C24 C23 123.6(10) . . ?
O4 C24 C23 117.8(6) . . ?
C34 C25 O4 122.8(6) . . ?
C34 C25 C26 123.8(7) . . ?
O4 C25 C26 113.4(7) . . ?
C27 C26 C25 118.8(7) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 121.7(7) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C33 119.4(7) . . ?
C27 C28 C29 122.0(7) . . ?
C33 C28 C29 118.5(7) . . ?
C30 C29 C28 120.8(7) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.8(8) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 120.3(8) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 122.8(6) . . ?
C31 C32 H32 118.6 . . ?
C33 C32 H32 118.6 . . ?
C32 C33 C28 116.6(6) . . ?
C32 C33 C34 125.2(5) . . ?
C28 C33 C34 118.1(6) . . ?
C25 C34 C33 117.3(6) . . ?
C25 C34 C35 116.3(6) . . ?
C33 C34 C35 126.3(5) . . ?
C23 C35 C36 116.1(6) . . ?
C23 C35 C34 119.3(6) . . ?
C36 C35 C34 124.6(5) . . ?
C20 C36 C35 121.7(6) . . ?
C20 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
F9' C37 F7' 107.2(8) . . ?
F9' C37 F8' 106.8(8) . . ?
F7' C37 F8' 106.7(8) . . ?
F7 C37 F9 107.2(6) . . ?
F7 C37 F8 106.6(7) . . ?
F9 C37 F8 105.3(6) . . ?
F7 C37 C38 112.8(8) . . ?
F9' C37 C38 108.5(12) . . ?
F7' C37 C38 111.9(12) . . ?
F8' C37 C38 115.3(10) . . ?
F9 C37 C38 113.1(7) . . ?
F8 C37 C38 111.3(7) . . ?
C54 C38 C39 121.5(6) . . ?
C54 C38 C37 118.3(5) . . ?
C39 C38 C37 120.2(6) . . ?
C40 C39 C38 118.1(6) . . ?
C40 C39 H39 120.9 . . ?
C38 C39 H39 120.9 . . ?
C39 C40 C41 121.0(6) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
C40 C41 C53 121.3(6) . . ?
C40 C41 C42 116.3(6) . . ?
C53 C41 C42 122.3(6) . . ?
O5 C42 O6 118.0(7) . . ?
O5 C42 C41 126.7(8) . . ?
O6 C42 C41 115.1(6) . . ?
O6 C43 C52 123.3(6) . . ?
O6 C43 C44 114.2(6) . . ?
C52 C43 C44 122.4(7) . . ?
C45 C44 C43 119.8(7) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 121.1(7) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 H45 119.5 . . ?
C45 C46 C47 122.2(7) . . ?
C45 C46 C51 119.8(7) . . ?
C47 C46 C51 118.0(8) . . ?
C48 C47 C46 122.1(7) . . ?
C48 C47 H47 119.0 . . ?
C46 C47 H47 119.0 . . ?
C47 C48 C49 119.4(8) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
C48 C49 C50 121.5(8) . . ?
C48 C49 H49 119.3 . . ?
C50 C49 H49 119.3 . . ?
C49 C50 C51 121.1(7) . . ?
C49 C50 H50 119.4 . . ?
C51 C50 H50 119.4 . . ?
C50 C51 C46 117.2(6) . . ?
C50 C51 C52 124.4(6) . . ?
C46 C51 C52 118.3(6) . . ?
C43 C52 C51 117.6(6) . . ?
C43 C52 C53 116.6(6) . . ?
C51 C52 C53 125.7(5) . . ?
C54 C53 C41 117.3(5) . . ?
C54 C53 C52 124.8(5) . . ?
C41 C53 C52 117.7(5) . . ?
C38 C54 C53 120.6(5) . . ?
C38 C54 H54 119.7 . . ?
C53 C54 H54 119.7 . . ?
C6 O2 C7 123.0(6) . . ?
C24 O4 C25 122.2(6) . . ?
C42 O6 C43 123.0(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.313(8) . ?
C1 F2 1.314(8) . ?
C1 F2' 1.316(9) . ?
C1 F3' 1.317(9) . ?
C1 F3 1.328(8) . ?
C1 F1' 1.333(9) . ?
C1 C2 1.496(13) . ?
C2 C18 1.384(9) . ?
C2 C3 1.389(12) . ?
C3 C4 1.359(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(11) . ?
C4 H4 0.9300 . ?
C5 C17 1.421(9) . ?
C5 C6 1.472(11) . ?
C6 O1 1.214(8) . ?
C6 O2 1.364(9) . ?
C7 O2 1.380(7) . ?
C7 C16 1.384(9) . ?
C7 C8 1.393(9) . ?
C8 C9 1.330(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.410(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(9) . ?
C10 C15 1.438(8) . ?
C11 C12 1.353(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.421(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.447(8) . ?
C16 C17 1.462(8) . ?
C17 C18 1.397(9) . ?
C18 H18 0.9300 . ?
C19 F5 1.309(9) . ?
C19 F6 1.320(9) . ?
C19 F4 1.340(8) . ?
C19 C20 1.467(11) . ?
C20 C36 1.382(8) . ?
C20 C21 1.410(10) . ?
C21 C22 1.355(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(10) . ?
C22 H22 0.9300 . ?
C23 C35 1.402(8) . ?
C23 C24 1.481(11) . ?
C24 O3 1.210(8) . ?
C24 O4 1.328(10) . ?
C25 C34 1.378(9) . ?
C25 O4 1.390(9) . ?
C25 C26 1.400(10) . ?
C26 C27 1.329(12) . ?
C26 H26 0.9300 . ?
C27 C28 1.417(12) . ?
C27 H27 0.9300 . ?
C28 C33 1.432(8) . ?
C28 C29 1.437(11) . ?
C29 C30 1.342(12) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.363(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.392(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.435(8) . ?
C34 C35 1.462(8) . ?
C35 C36 1.409(8) . ?
C36 H36 0.9300 . ?
C37 F7 1.310(7) . ?
C37 F9' 1.313(8) . ?
C37 F7' 1.316(8) . ?
C37 F8' 1.317(8) . ?
C37 F9 1.319(7) . ?
C37 F8 1.330(7) . ?
C37 C38 1.504(9) . ?
C38 C54 1.378(8) . ?
C38 C39 1.394(9) . ?
C39 C40 1.371(10) . ?
C39 H39 0.9300 . ?
C40 C41 1.378(9) . ?
C40 H40 0.9300 . ?
C41 C53 1.404(8) . ?
C41 C42 1.469(9) . ?
C42 O5 1.194(8) . ?
C42 O6 1.370(9) . ?
C43 O6 1.373(8) . ?
C43 C52 1.378(8) . ?
C43 C44 1.408(10) . ?
C44 C45 1.335(11) . ?
C44 H44 0.9300 . ?
C45 C46 1.408(11) . ?
C45 H45 0.9300 . ?
C46 C47 1.422(11) . ?
C46 C51 1.425(9) . ?
C47 C48 1.354(12) . ?
C47 H47 0.9300 . ?
C48 C49 1.363(11) . ?
C48 H48 0.9300 . ?
C49 C50 1.369(9) . ?
C49 H49 0.9300 . ?
C50 C51 1.415(9) . ?
C50 H50 0.9300 . ?
C51 C52 1.437(9) . ?
C52 C53 1.478(8) . ?
C53 C54 1.390(8) . ?
C54 H54 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 O2 0.93 2.57 3.496(9) 172.2 2_655 yes
C8 H8 O2 0.93 2.57 3.496(9) 172.2 2_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C18 -167.4(10) . . . . ?
F2 C1 C2 C18 70.4(12) . . . . ?
F2' C1 C2 C18 8(2) . . . . ?
F3' C1 C2 C18 -123.5(18) . . . . ?
F3 C1 C2 C18 -49.7(11) . . . . ?
F1' C1 C2 C18 122.7(16) . . . . ?
F1 C1 C2 C3 14.6(12) . . . . ?
F2 C1 C2 C3 -107.7(12) . . . . ?
F2' C1 C2 C3 -169.7(19) . . . . ?
F3' C1 C2 C3 58(2) . . . . ?
F3 C1 C2 C3 132.2(10) . . . . ?
F1' C1 C2 C3 -55.3(17) . . . . ?
C18 C2 C3 C4 4.3(13) . . . . ?
C1 C2 C3 C4 -177.7(8) . . . . ?
C2 C3 C4 C5 -3.0(13) . . . . ?
C3 C4 C5 C17 -1.5(12) . . . . ?
C3 C4 C5 C6 174.3(8) . . . . ?
C4 C5 C6 O1 6.9(11) . . . . ?
C17 C5 C6 O1 -177.2(7) . . . . ?
C4 C5 C6 O2 -168.3(6) . . . . ?
C17 C5 C6 O2 7.5(10) . . . . ?
O2 C7 C8 C9 179.5(6) . . . . ?
C16 C7 C8 C9 -3.0(10) . . . . ?
C7 C8 C9 C10 -3.5(11) . . . . ?
C8 C9 C10 C11 -173.6(7) . . . . ?
C8 C9 C10 C15 1.8(10) . . . . ?
C9 C10 C11 C12 172.9(7) . . . . ?
C15 C10 C11 C12 -2.4(10) . . . . ?
C10 C11 C12 C13 -1.3(11) . . . . ?
C11 C12 C13 C14 3.7(11) . . . . ?
C12 C13 C14 C15 -2.3(11) . . . . ?
C13 C14 C15 C10 -1.3(9) . . . . ?
C13 C14 C15 C16 -179.0(6) . . . . ?
C11 C10 C15 C14 3.6(9) . . . . ?
C9 C10 C15 C14 -171.9(6) . . . . ?
C11 C10 C15 C16 -178.5(6) . . . . ?
C9 C10 C15 C16 5.9(9) . . . . ?
O2 C7 C16 C15 -172.4(5) . . . . ?
C8 C7 C16 C15 10.3(9) . . . . ?
O2 C7 C16 C17 8.1(9) . . . . ?
C8 C7 C16 C17 -169.2(6) . . . . ?
C14 C15 C16 C7 166.2(6) . . . . ?
C10 C15 C16 C7 -11.4(8) . . . . ?
C14 C15 C16 C17 -14.3(10) . . . . ?
C10 C15 C16 C17 168.0(6) . . . . ?
C4 C5 C17 C18 4.4(10) . . . . ?
C6 C5 C17 C18 -171.2(6) . . . . ?
C4 C5 C17 C16 -179.0(6) . . . . ?
C6 C5 C17 C16 5.4(9) . . . . ?
C7 C16 C17 C18 163.2(6) . . . . ?
C15 C16 C17 C18 -16.3(10) . . . . ?
C7 C16 C17 C5 -13.0(9) . . . . ?
C15 C16 C17 C5 167.5(6) . . . . ?
C3 C2 C18 C17 -1.2(11) . . . . ?
C1 C2 C18 C17 -179.2(7) . . . . ?
C5 C17 C18 C2 -3.1(10) . . . . ?
C16 C17 C18 C2 -179.3(6) . . . . ?
F5 C19 C20 C36 26.2(11) . . . . ?
F6 C19 C20 C36 -96.3(8) . . . . ?
F4 C19 C20 C36 145.6(7) . . . . ?
F5 C19 C20 C21 -158.2(7) . . . . ?
F6 C19 C20 C21 79.3(9) . . . . ?
F4 C19 C20 C21 -38.8(10) . . . . ?
C36 C20 C21 C22 -3.9(11) . . . . ?
C19 C20 C21 C22 -179.6(8) . . . . ?
C20 C21 C22 C23 2.9(12) . . . . ?
C21 C22 C23 C35 2.2(11) . . . . ?
C21 C22 C23 C24 -174.4(7) . . . . ?
C22 C23 C24 O3 -5.2(11) . . . . ?
C35 C23 C24 O3 178.1(7) . . . . ?
C22 C23 C24 O4 170.9(7) . . . . ?
C35 C23 C24 O4 -5.8(10) . . . . ?
C34 C25 C26 C27 1.6(12) . . . . ?
O4 C25 C26 C27 -177.9(7) . . . . ?
C25 C26 C27 C28 3.8(12) . . . . ?
C26 C27 C28 C33 -2.1(11) . . . . ?
C26 C27 C28 C29 174.8(7) . . . . ?
C27 C28 C29 C30 -173.7(7) . . . . ?
C33 C28 C29 C30 3.2(11) . . . . ?
C28 C29 C30 C31 0.8(13) . . . . ?
C29 C30 C31 C32 -2.4(12) . . . . ?
C30 C31 C32 C33 -0.2(11) . . . . ?
C31 C32 C33 C28 4.1(10) . . . . ?
C31 C32 C33 C34 -179.8(6) . . . . ?
C27 C28 C33 C32 171.5(6) . . . . ?
C29 C28 C33 C32 -5.4(9) . . . . ?
C27 C28 C33 C34 -4.8(9) . . . . ?
C29 C28 C33 C34 178.2(6) . . . . ?
O4 C25 C34 C33 171.1(6) . . . . ?
C26 C25 C34 C33 -8.4(10) . . . . ?
O4 C25 C34 C35 -8.2(9) . . . . ?
C26 C25 C34 C35 172.3(6) . . . . ?
C32 C33 C34 C25 -166.3(6) . . . . ?
C28 C33 C34 C25 9.7(8) . . . . ?
C32 C33 C34 C35 12.8(9) . . . . ?
C28 C33 C34 C35 -171.2(6) . . . . ?
C22 C23 C35 C36 -5.9(9) . . . . ?
C24 C23 C35 C36 170.7(6) . . . . ?
C22 C23 C35 C34 175.6(6) . . . . ?
C24 C23 C35 C34 -7.8(9) . . . . ?
C25 C34 C35 C23 14.5(8) . . . . ?
C33 C34 C35 C23 -164.7(6) . . . . ?
C25 C34 C35 C36 -163.9(6) . . . . ?
C33 C34 C35 C36 16.9(9) . . . . ?
C21 C20 C36 C35 0.0(10) . . . . ?
C19 C20 C36 C35 175.7(6) . . . . ?
C23 C35 C36 C20 4.8(8) . . . . ?
C34 C35 C36 C20 -176.8(6) . . . . ?
F7 C37 C38 C54 166.9(12) . . . . ?
F9' C37 C38 C54 -109.8(19) . . . . ?
F7' C37 C38 C54 132.1(19) . . . . ?
F8' C37 C38 C54 10(2) . . . . ?
F9 C37 C38 C54 -71.3(14) . . . . ?
F8 C37 C38 C54 47.1(13) . . . . ?
F7 C37 C38 C39 -13.6(14) . . . . ?
F9' C37 C38 C39 69.7(19) . . . . ?
F7' C37 C38 C39 -48(2) . . . . ?
F8' C37 C38 C39 -171(2) . . . . ?
F9 C37 C38 C39 108.2(14) . . . . ?
F8 C37 C38 C39 -133.4(12) . . . . ?
C54 C38 C39 C40 0.0(10) . . . . ?
C37 C38 C39 C40 -179.5(6) . . . . ?
C38 C39 C40 C41 -0.2(10) . . . . ?
C39 C40 C41 C53 1.7(10) . . . . ?
C39 C40 C41 C42 -174.3(6) . . . . ?
C40 C41 C42 O5 -8.8(10) . . . . ?
C53 C41 C42 O5 175.3(6) . . . . ?
C40 C41 C42 O6 167.1(6) . . . . ?
C53 C41 C42 O6 -8.8(9) . . . . ?
O6 C43 C44 C45 179.3(7) . . . . ?
C52 C43 C44 C45 1.9(11) . . . . ?
C43 C44 C45 C46 3.5(12) . . . . ?
C44 C45 C46 C47 176.7(7) . . . . ?
C44 C45 C46 C51 -0.6(11) . . . . ?
C45 C46 C47 C48 -174.2(8) . . . . ?
C51 C46 C47 C48 3.2(12) . . . . ?
C46 C47 C48 C49 4.2(14) . . . . ?
C47 C48 C49 C50 -6.9(14) . . . . ?
C48 C49 C50 C51 2.0(12) . . . . ?
C49 C50 C51 C46 5.3(10) . . . . ?
C49 C50 C51 C52 -177.8(7) . . . . ?
C45 C46 C51 C50 169.8(7) . . . . ?
C47 C46 C51 C50 -7.7(10) . . . . ?
C45 C46 C51 C52 -7.3(10) . . . . ?
C47 C46 C51 C52 175.2(6) . . . . ?
O6 C43 C52 C51 173.1(6) . . . . ?
C44 C43 C52 C51 -9.7(10) . . . . ?
O6 C43 C52 C53 -8.7(9) . . . . ?
C44 C43 C52 C53 168.5(6) . . . . ?
C50 C51 C52 C43 -164.7(6) . . . . ?
C46 C51 C52 C43 12.1(9) . . . . ?
C50 C51 C52 C53 17.2(10) . . . . ?
C46 C51 C52 C53 -165.9(6) . . . . ?
C40 C41 C53 C54 -3.0(9) . . . . ?
C42 C41 C53 C54 172.8(6) . . . . ?
C40 C41 C53 C52 -179.1(6) . . . . ?
C42 C41 C53 C52 -3.3(8) . . . . ?
C43 C52 C53 C54 -163.9(6) . . . . ?
C51 C52 C53 C54 14.2(9) . . . . ?
C43 C52 C53 C41 11.9(8) . . . . ?
C51 C52 C53 C41 -170.0(6) . . . . ?
C39 C38 C54 C53 -1.4(9) . . . . ?
C37 C38 C54 C53 178.1(5) . . . . ?
C41 C53 C54 C38 2.8(8) . . . . ?
C52 C53 C54 C38 178.6(6) . . . . ?
O1 C6 O2 C7 171.0(6) . . . . ?
C5 C6 O2 C7 -13.4(9) . . . . ?
C16 C7 O2 C6 5.8(9) . . . . ?
C8 C7 O2 C6 -176.6(6) . . . . ?
O3 C24 O4 C25 -170.9(7) . . . . ?
C23 C24 O4 C25 12.8(10) . . . . ?
C34 C25 O4 C24 -5.8(10) . . . . ?
C26 C25 O4 C24 173.7(7) . . . . ?
O5 C42 O6 C43 -170.8(6) . . . . ?
C41 C42 O6 C43 12.9(8) . . . . ?
C52 C43 O6 C42 -4.3(10) . . . . ?
C44 C43 O6 C42 178.3(6) . . . . ?
